Vacation rentals with a hot tub in Berkshire County

Our family (and dog) stayed for Thanksgiving weekend and we had an amazing time. There is a gorgeous 0.8 mile walk in the woods right from the back of the house. We loved the hot tub! And we made fires in the fireplace every day. The kitchen was well appointed and we were easily able to cook our Thanksgiving dinner. We were close to Great Barrington, Lenox, and Stockbridge. Great food. Great shopping. Guidos in Pittsfield was great for food shopping. The house and setting were perfect. We will definitely be back!

This amazing, spacious, luxurious house is better than the photos. It had everything we wanted and more. Privacy, quiet, beautiful views of the land and woods, walking paths with a little bench by a creek. Gorgeous kitchen fully stocked with plenty of plates, cooking gear and utensils. Modern yet comfortable and cozy design throughout. Beds were fabulous. Sparkling clean bathrooms. And tons of games and TVs to keep everyone entertained. Plus a sauna is built into one of the bathrooms. And since we brought our 90 year old mother, the ramp to the back door was used and appreciated. There is something for everyone here.

House was well appointed. There is tons of space and little nooks if you need need some alone time. There are three places with desks that have privacy if you need to have a spot to work. Beautiful surroundings, very peaceful. Short drive to town with lots of choices for eating and shopping. Highly recommend. Lucas was very responsive to any questions we had. House book was very detailed and answered any questions we had.

We loved this beautifully decorated home. When we arrived the wood-burning stove and hot tub were already on! It was a very welcoming environment and very close to great barrington, MA and Hudson, NY. We would love to come back and spend either a winter or summer holiday here.

We had a great stay at Michelle’s place. It was very conveniently located to the base of Jiminy Peak, which made getting to and from the mountain very easy. The house was very well appointed and had everything we needed. We used the fireplace twice and it was super easy. Having access to the facilities at The Country Inn at Jiminy Peak was great as I am injured and can’t ski currently, so instead I went to the gym each day. My family didn’t want to leave and my kids are asking when we can go back!

We loved staying here with our family. It worked out perfectly having our daughter’s family on the one side of the house so if the baby cried it wouldn’t wake anyone up. A pack and play was also provided by Justin so we had a place for the baby downstairs as well. The house was roomy and comfortable for everyone. The hot tub wasn’t working right away but they let us know and had it fixed so we were able to use it during our trip. We would definitely stay here again and try it in warmer weather so we could use the pool as well. Thank you for a wonderful place to stay

We had a great stay in GB. Annie, Reid and Lauren were super responsive with any questions we had. They were also extremely flexible with check-in and check-out time which was so nice. The house fit 10 of us great and had everything we needed! Was very clean and comfortable for adults and kids. The only thing about the location is we thought it was 10 minutes from butternut but one of the roads was closed due to a bridge being icy so we had to go around to get there. Only about 20 mins which wasn’t a big deal at all! Restaurant recommendations were great as well. Highly recommend and hope to be back! Thank you all!

We had the most wonderful stay. Having traveled from Rhode Island for an escape from the holidays we had actually rented a hotel in Germantown initially. Without going into too much detail the hotel was not up to our standards. After one night there we began looking into alternatives. we found Hilltop and it looked perfect. Quickly, we were able to secure a booking for the remainder of our trip. Very responsive interaction throughout booking. It proved to be a peaceful oasis for the remainder of our trip and was a very memorable experience. The modern aesthetic was fantastic and we appreciated the architectural thoughtfulness which went into the design. It even snowed during our stay at the higher elevation the property is situated on. We were already planning a return visit to experience the surroundings in the summer. Thank you for sharing your place with us!

Immaculate, cozy cabin that’s the perfect balance of modern and rustic. My partner and I loved it so much, the view during fall was gorgeous! The record player, the wood fired hot tub - every little part of the experience was so relaxing. The Berkshires make for a stunning backdrop and you have tons of great restaurants and cafes nearby. Highly recommend, the hosts have been so thoughtful with how they designed this space.

I genuinely can’t say enough about this place. It’s absolutely beautiful! Thoughtfully designed, super clean, and filled with the kind of details that make you feel at home. The plants throughout the space add such a calm, lived-in vibe, and the views are unreal. The outdoor areas were perfect for lounging while it was warmer (we visited mid April) but it’s definitely a spot you can enjoy in any season! The bathrooms and appliances, the WHOLE place is all super modern and brand new, but still feels really cozy and welcoming. And the host are truly one of the best we’ve ever encountered. So kind, so responsive, and even sent over local event links to help us find cool things to do in the area on Easter Sunday! We’ve stayed in a lot of Airbnbs over the years, and this one is easily in our top 5. Zero regrets booking it and we’re already looking forward to coming back!

This place is an absolute gem. Definitely one of our favorite Airbnb‘s we’ve ever had the privilege of visiting. The setting is spectacular, and the house is so charming and well equipped. Our kids had a blast and we definitely enjoyed the Jacuzzi in the master bathroom. It’s easy to tell that this is a treasured family cabin, lovingly tended to. Very accessible to Great Barrington and loads of wonderful hikes nearby. I highly recommend!

Definitely an amazing place, beautiful! But secluded make sure to stock up on groceries and essentials before arriving nearest market is about 16 minutes away. Overall great stay!

AMAZING! Some friends and I escaped the city for 3 days and stayed at this cabin. We will definitely be returning. The place was huge and so cute. Joy was more than accommodating. The hot tub was huge and clean. The wood burning fire places were so cute. Overall amazing place to say I would 1000% recommend.